SK580690A3 - Isoindolone derivatives, process of their preparation and their use as intermediate products - Google Patents

Isoindolone derivatives, process of their preparation and their use as intermediate products Download PDF

Info

Publication number: SK580690A3
Authority: SK; Slovakia
Prior art keywords: group; isoindolone; alkyl; hydrogen atom; phenyl
Prior art date: 1989-11-23

Application number

SK5806-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK278474B6 (en

Inventor

Marie-Christine Dubroeucq

Claude Moutonnier

Jean-Francois Peyronel

Michel Tabart

Alain Truchon

Original Assignee

Rhone Poulenc Sante

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-11-23

Filing date

1990-11-22

Publication date

1997-07-09

1990-11-22 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1997-07-09 Publication of SK278474B6 publication Critical patent/SK278474B6/sk

1997-07-09 Publication of SK580690A3 publication Critical patent/SK580690A3/sk

Links

XTBAPWCYTNCZTO-UHFFFAOYSA-N isoindol-1-one Chemical class C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 title claims description 43
238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 16
239000013067 intermediate product Substances 0.000 title 1
239000011541 reaction mixture Substances 0.000 claims description 76
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
229910052757 nitrogen Inorganic materials 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 27
238000010992 reflux Methods 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
125000004663 dialkyl amino group Chemical group 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 20
BGXMXYKDFFAEKA-UHFFFAOYSA-N 1,2,3,3a,5,6,7,7a-octahydroisoindol-4-one Chemical compound O=C1CCCC2CNCC12 BGXMXYKDFFAEKA-UHFFFAOYSA-N 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
238000009835 boiling Methods 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
230000002378 acidificating effect Effects 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 7
PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
229920002554 vinyl polymer Polymers 0.000 claims description 7
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
BSZYCEVZKJVXAF-UHFFFAOYSA-N 2-(nitromethyl)-6-oxocyclohexane-1-carbaldehyde Chemical compound [O-][N+](=O)CC1CCCC(=O)C1C=O BSZYCEVZKJVXAF-UHFFFAOYSA-N 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
238000006683 Mannich reaction Methods 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 3
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
WYBVWRBMKAWGRK-UHFFFAOYSA-N 7,7-diphenyl-2,3,3a,5,6,7a-hexahydro-1h-isoindol-4-one Chemical compound C12CNCC2C(=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 WYBVWRBMKAWGRK-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
125000005242 carbamoyl alkyl group Chemical group 0.000 claims 2
229910052799 carbon Inorganic materials 0.000 claims 2
125000003367 polycyclic group Chemical group 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 192
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
239000000243 solution Substances 0.000 description 151
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 84
239000000203 mixture Substances 0.000 description 81
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000013078 crystal Substances 0.000 description 48
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
229910052943 magnesium sulfate Inorganic materials 0.000 description 42
235000019341 magnesium sulphate Nutrition 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
-1 polycyclic heterocyclic hydrocarbon Chemical class 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
239000002245 particle Substances 0.000 description 33
239000000741 silica gel Substances 0.000 description 33
229910002027 silica gel Inorganic materials 0.000 description 33
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000012074 organic phase Substances 0.000 description 27
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000012452 mother liquor Substances 0.000 description 24
239000000047 product Substances 0.000 description 23
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 18
239000012153 distilled water Substances 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 17
239000007787 solid Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
KZMSVLOJRPGWDY-UHFFFAOYSA-N n-(butoxymethyl)-1-phenyl-n-(trimethylsilylmethyl)methanamine Chemical compound CCCCOCN(C[Si](C)(C)C)CC1=CC=CC=C1 KZMSVLOJRPGWDY-UHFFFAOYSA-N 0.000 description 11
CIJLMNDNUOEELM-UHFFFAOYSA-N 7,7-diphenyl-2,3,3a,5,6,7a-hexahydro-1h-isoindol-4-one;hydrochloride Chemical compound Cl.C12CNCC2C(=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 CIJLMNDNUOEELM-UHFFFAOYSA-N 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
238000002329 infrared spectrum Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 8
239000006260 foam Substances 0.000 description 8
CIJLMNDNUOEELM-CJRXIRLBSA-N (3ar,7ar)-7,7-diphenyl-2,3,3a,5,6,7a-hexahydro-1h-isoindol-4-one;hydrochloride Chemical compound Cl.O=C([C@H]1CNC[C@H]11)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 CIJLMNDNUOEELM-CJRXIRLBSA-N 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000002609 medium Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
DQSBXVQJLSMPKA-UHFFFAOYSA-N 2-[2-(dimethylamino)phenyl]acetic acid Chemical compound CN(C)C1=CC=CC=C1CC(O)=O DQSBXVQJLSMPKA-UHFFFAOYSA-N 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
YDTCAOIRGWQXAI-UHFFFAOYSA-N 2-benzyl-7,7-diphenyl-1,3,3a,5,6,7a-hexahydroisoindol-4-one Chemical compound C1C2C(=O)CCC(C=3C=CC=CC=3)(C=3C=CC=CC=3)C2CN1CC1=CC=CC=C1 YDTCAOIRGWQXAI-UHFFFAOYSA-N 0.000 description 5
NALFFVVWCWBHNH-UHFFFAOYSA-N 7,7-bis(3-fluorophenyl)-2,3,3a,5,6,7a-hexahydro-1h-isoindol-4-one;hydrochloride Chemical compound Cl.FC1=CC=CC(C2(C3CNCC3C(=O)CC2)C=2C=C(F)C=CC=2)=C1 NALFFVVWCWBHNH-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
244000309464 bull Species 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
FURUSGMMMFSWDW-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]acetic acid Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1CC(O)=O FURUSGMMMFSWDW-UHFFFAOYSA-N 0.000 description 4
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 4
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical class C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
230000008030 elimination Effects 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
USRCWTXXFCGGNR-UHFFFAOYSA-N (7,7-diphenyl-1,4-dioxaspiro[4.5]decan-6-yl)methanamine Chemical compound C1CCC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C(CN)C21OCCO2 USRCWTXXFCGGNR-UHFFFAOYSA-N 0.000 description 3
QQPIWTIJSNRRQR-UHFFFAOYSA-N 2,2-bis(2-fluorophenyl)acetaldehyde Chemical compound FC1=CC=CC=C1C(C=O)C1=CC=CC=C1F QQPIWTIJSNRRQR-UHFFFAOYSA-N 0.000 description 3
OPJBBPPWNOJJCC-UHFFFAOYSA-N 2,2-bis(3-methylphenyl)acetaldehyde Chemical compound CC1=CC=CC(C(C=O)C=2C=C(C)C=CC=2)=C1 OPJBBPPWNOJJCC-UHFFFAOYSA-N 0.000 description 3
IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 description 3
NFIIDFQRGXRFOI-UHFFFAOYSA-N 2-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenyl]acetic acid Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC=C1CC(O)=O NFIIDFQRGXRFOI-UHFFFAOYSA-N 0.000 description 3
UMWCKEWDYGSKNL-UHFFFAOYSA-N 2-benzyl-7,7-diphenyl-1,3,3a,7a-tetrahydroisoindol-4-one Chemical compound C1C2C(=O)C=CC(C=3C=CC=CC=3)(C=3C=CC=CC=3)C2CN1CC1=CC=CC=C1 UMWCKEWDYGSKNL-UHFFFAOYSA-N 0.000 description 3
QSNJSTSTWGYPDS-UHFFFAOYSA-N 2-oxo-5,5-diphenylcyclohexane-1-carbaldehyde Chemical compound C1CC(=O)C(C=O)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 QSNJSTSTWGYPDS-UHFFFAOYSA-N 0.000 description 3
PGNRUDSXTZSZON-UHFFFAOYSA-N 4,4-bis(3-methylphenyl)cyclohex-2-en-1-one Chemical compound CC1=CC=CC(C2(C=CC(=O)CC2)C=2C=C(C)C=CC=2)=C1 PGNRUDSXTZSZON-UHFFFAOYSA-N 0.000 description 3
LUFGFXHHSGISSL-UHFFFAOYSA-N 4,4-diphenylcyclohex-2-en-1-one Chemical compound C1=CC(=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 LUFGFXHHSGISSL-UHFFFAOYSA-N 0.000 description 3
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210000003169 central nervous system Anatomy 0.000 description 1
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239000012230 colorless oil Substances 0.000 description 1
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239000006071 cream Substances 0.000 description 1
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230000002526 effect on cardiovascular system Effects 0.000 description 1
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239000000499 gel Substances 0.000 description 1
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ZMPYQGQHGLLBQI-UHFFFAOYSA-M magnesium;chlorobenzene;bromide Chemical compound [Mg+2].[Br-].ClC1=CC=C[C-]=C1 ZMPYQGQHGLLBQI-UHFFFAOYSA-M 0.000 description 1
DTKMKZYEOXZPQZ-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=C[C-]=C1 DTKMKZYEOXZPQZ-UHFFFAOYSA-M 0.000 description 1
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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238000000053 physical method Methods 0.000 description 1
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239000012265 solid product Substances 0.000 description 1
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230000002048 spasmolytic effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
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239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
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150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

SK5806-90A 1989-11-23 1990-11-22 Isoindolone derivatives, process of their preparation and their use as intermediate products SK580690A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8915407A FR2654726B1 (fr)	1989-11-23	1989-11-23	Nouveaux derives de l'isoindolone et leur preparation.

Publications (2)

Publication Number	Publication Date
SK278474B6 SK278474B6 (en)	1997-07-09
SK580690A3 true SK580690A3 (en)	1997-07-09

Family

ID=9387708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK5806-90A SK580690A3 (en)	1989-11-23	1990-11-22	Isoindolone derivatives, process of their preparation and their use as intermediate products

Country Status (23)

Country	Link
US (1)	US5112988A (pt)
EP (1)	EP0430771B1 (pt)
JP (1)	JPH03176468A (pt)
KR (1)	KR910009660A (pt)
AT (1)	ATE108774T1 (pt)
AU (1)	AU635984B2 (pt)
CA (1)	CA2030570A1 (pt)
DE (1)	DE69010851T2 (pt)
DK (1)	DK0430771T3 (pt)
ES (1)	ES2057488T3 (pt)
FI (1)	FI94627C (pt)
FR (1)	FR2654726B1 (pt)
HU (1)	HU214574B (pt)
IE (1)	IE64737B1 (pt)
IL (1)	IL96447A (pt)
NO (1)	NO174148C (pt)
NZ (1)	NZ236175A (pt)
PL (2)	PL164955B1 (pt)
PT (1)	PT95983B (pt)
RU (1)	RU2104269C1 (pt)
SK (1)	SK580690A3 (pt)
YU (1)	YU47437B (pt)
ZA (1)	ZA909370B (pt)

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FR2709752B1 (fr) *	1993-07-30	1995-10-06	Rhone Poulenc Rorer Sa	Nouveaux dérivés de perhydroisoindole, leur préparation et les compositions pharmaceutiques qui les contiennent.
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FR2728169A1 (fr)	1994-12-19	1996-06-21	Oreal	Utilisation d'un antagoniste de substance p pour le traitement des prurits et des dysesthesies oculaires ou palpebrales
FR2728165A1 (fr)	1994-12-19	1996-06-21	Oreal	Utilisation d'un antagoniste de substance p pour le traitement des rougeurs cutanees d'origine neurogene
FR2729954B1 (fr)	1995-01-30	1997-08-01	Sanofi Sa	Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant
FR2741262B1 (fr)	1995-11-20	1999-03-05	Oreal	Utilisation d'un antagoniste de tnf-alpha pour le traitement des rougeurs cutanees d'origine neurogene
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JP5258561B2 (ja)	2005-07-15	2013-08-07	アルバニーモレキュラーリサーチ，インコーポレイテッド	アリール置換およびヘテロアリール置換テトラヒドロベンズアゼピンならびにノルエピネフリン、ドーパミンおよびセロトニンの再取り込みを遮断するためのその使用
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JP4611444B2 (ja)	2007-01-10	2011-01-12	イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー	ポリ（ａｄｐ−リボース）ポリメラーゼ（ｐａｒｐ）阻害剤としてのアミド置換インダゾール
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US9156812B2 (en)	2008-06-04	2015-10-13	Bristol-Myers Squibb Company	Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine
AR071997A1 (es)	2008-06-04	2010-07-28	Bristol Myers Squibb Co	Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina
US8691825B2 (en)	2009-04-01	2014-04-08	Merck Sharp & Dohme Corp.	Inhibitors of AKT activity
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AU2010247849B2 (en)	2009-05-12	2015-11-19	Albany Molecular Research, Inc.	Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof
US8815894B2 (en)	2009-05-12	2014-08-26	Bristol-Myers Squibb Company	Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof
JP5099731B1 (ja)	2009-10-14	2012-12-19	メルク・シャープ・アンド・ドーム・コーポレーション	ｐ５３活性を増大する置換ピペリジン及びその使用
CA2788155C (en) *	2010-01-27	2018-04-24	AB Pharma Ltd.	Polyheterocyclic compounds highly potent as hcv inhibitors
US8518907B2 (en)	2010-08-02	2013-08-27	Merck Sharp & Dohme Corp.	RNA interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (CTNNB1) gene expression using short interfering nucleic acid (siNA)
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US2858314A (en) *	1954-06-07	1958-10-28	Georgian Vlasios	Hydrocarbazolenines
US4042707A (en) *	1976-02-19	1977-08-16	E. I. Du Pont De Nemours And Company	3α-Arylhydroisoindoles
US4494547A (en) *	1981-03-30	1985-01-22	North Carolina Central University	2H-isoindolediones, their synthesis and use as radiosensitizers

1989
- 1989-11-23 FR FR8915407A patent/FR2654726B1/fr not_active Expired - Lifetime
1990
- 1990-11-20 US US07/616,044 patent/US5112988A/en not_active Expired - Fee Related
- 1990-11-21 NZ NZ236175A patent/NZ236175A/xx unknown
- 1990-11-22 KR KR1019900019099A patent/KR910009660A/ko not_active Abandoned
- 1990-11-22 CA CA002030570A patent/CA2030570A1/fr not_active Abandoned
- 1990-11-22 AU AU66828/90A patent/AU635984B2/en not_active Ceased
- 1990-11-22 ES ES90403300T patent/ES2057488T3/es not_active Expired - Lifetime
- 1990-11-22 AT AT90403300T patent/ATE108774T1/de not_active IP Right Cessation
- 1990-11-22 NO NO905067A patent/NO174148C/no unknown
- 1990-11-22 HU HU907249A patent/HU214574B/hu not_active IP Right Cessation
- 1990-11-22 IE IE423490A patent/IE64737B1/en not_active IP Right Cessation
- 1990-11-22 DE DE69010851T patent/DE69010851T2/de not_active Expired - Fee Related
- 1990-11-22 ZA ZA909370A patent/ZA909370B/xx unknown
- 1990-11-22 EP EP90403300A patent/EP0430771B1/fr not_active Expired - Lifetime
- 1990-11-22 JP JP2320570A patent/JPH03176468A/ja active Pending
- 1990-11-22 DK DK90403300.8T patent/DK0430771T3/da active
- 1990-11-22 FI FI905770A patent/FI94627C/fi not_active IP Right Cessation
- 1990-11-22 IL IL9644790A patent/IL96447A/en not_active IP Right Cessation
- 1990-11-22 SK SK5806-90A patent/SK580690A3/sk unknown
- 1990-11-23 PL PL90301462A patent/PL164955B1/pl unknown
- 1990-11-23 PT PT95983A patent/PT95983B/pt not_active IP Right Cessation
- 1990-11-23 YU YU223590A patent/YU47437B/sh unknown
- 1990-11-23 PL PL90287908A patent/PL164973B1/pl unknown
1992
- 1992-12-01 RU RU92004482A patent/RU2104269C1/ru active

Also Published As

Publication number	Publication date
HU907249D0 (en)	1991-05-28
SK278474B6 (en)	1997-07-09
HUT55756A (en)	1991-06-28
PT95983B (pt)	1998-01-30
YU223590A (sh)	1993-05-28
DE69010851D1 (de)	1994-08-25
EP0430771A1 (fr)	1991-06-05
IE64737B1 (en)	1995-09-06
NZ236175A (en)	1993-03-26
KR910009660A (ko)	1991-06-28
IE904234A1 (en)	1991-06-05
NO174148C (no)	1994-03-23
IL96447A (en)	1995-03-15
FI905770A0 (fi)	1990-11-22
YU47437B (sh)	1995-03-27
RU2104269C1 (ru)	1998-02-10
IL96447A0 (en)	1991-08-16
PL287908A1 (en)	1991-12-02
JPH03176468A (ja)	1991-07-31
PL164973B1 (pl)	1994-10-31
FI94627B (fi)	1995-06-30
FR2654726B1 (fr)	1992-02-14
NO905067D0 (no)	1990-11-22
CA2030570A1 (fr)	1991-05-24
ZA909370B (en)	1991-10-30
US5112988A (en)	1992-05-12
PL164955B1 (en)	1994-10-31
PT95983A (pt)	1991-09-13
FR2654726A1 (fr)	1991-05-24
DK0430771T3 (da)	1994-08-29
FI905770L (fi)	1991-05-24
NO174148B (no)	1993-12-13
ES2057488T3 (es)	1994-10-16
ATE108774T1 (de)	1994-08-15
EP0430771B1 (fr)	1994-07-20
HU214574B (hu)	1998-04-28
FI94627C (fi)	1995-10-10
AU635984B2 (en)	1993-04-08
NO905067L (no)	1991-05-24
DE69010851T2 (de)	1994-11-24
AU6682890A (en)	1991-05-30

Publication	Publication Date	Title
SK580690A3 (en)	1997-07-09	Isoindolone derivatives, process of their preparation and their use as intermediate products
RU2012559C1 (ru)	1994-05-15	Производные изоиндолона в виде (3 аr, 7 аr)- или (3 аrs, 7 аrs)-форм или их смесей или их гидрохлориды, являющиеся антагонистами вещества р
US5508433A (en)	1996-04-16	Derivatives of perhydroisoindole and preparation thereof
US5451601A (en)	1995-09-19	Perhydroisoindole derivatives and pharmaceutical compositions containing them
KR100475206B1 (ko)	2005-12-16	사이클릭및헤테로사이클릭N-치환된α-이미노하이드록삼산및카복실산
AU653033B2 (en)	1994-09-15	Novel derivatives of thiopyranopyrrole, their preparation and pharmaceutical compositions containing them
FI105023B (fi)	2000-05-31	Menetelmä terapeuttisesti käyttökelpoisten difenyyli-4-perhydroisoindolijohdannaisten valmistamiseksi
CA1076142A (en)	1980-04-22	Substituted butyrophenone o-(2-aminoethyl) oxime derivatives
US5463077A (en)	1995-10-31	Perhydroisoindole derivatives and preparation
JP2003048894A (ja)	2003-02-21	イソインドリノン誘導体のラセミ生成物を構成するエナンチオマーの分離に用いる修飾されたパークルタイプの相
CA1063106A (en)	1979-09-25	Pharmacologically active pyrrolodiazepines
Giri et al.	1992	Synthesis of Indolo [2, 3-a] Ouinolizidin-2-One
FR2709752A1 (fr)	1995-03-17	Nouveaux dérivés de perhydroisoindole, leur préparation et les compositions pharmaceutiques qui les contiennent.
JPH0381274A (ja)	1991-04-05	ナフタレン誘導体の製法及びその合成中間体